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Product Citations

Product Citations

Anita Marfavi ; Liam D. Adair ; Elizabeth J. New , et al. DOI:

Abstract: Two novel chromenylium-based probes were developed by functionalisation of the 5-position of the xanthene core with either a para-N-methyldiaminoacetic acid (MIDA) boronate ester (CRpMD) or closo‑1,7-carborane (CRmCB). CRpMD revealed near-infrared emission at 655 nm, demonstrating a bathochromic shift compared to the analogous phenyl derivative (CRPh). Both boron-containing probes were found to be sensitive to changes in acidic pH, with CRpMD also displaying a dual fluorescence response at alkaline pH (pKa1 = 2.40 and pKa2 = 9.16). CRmCB showed a ca. 3-fold increase in fluorescence intensity at 638 nm from pH 7.01 to 2.00, with a pKa = 2.08. Moreover, CRpMD and CRmCB were successfully taken up by A549 lung cancer cells to assess their intracellular biodistributions, thereby showcasing the future potential of these probes for time-resolved pH measurements using confocal microscopy.

Keywords: Near-infrared ; Fluorescence microscopy ; Fluorescent probes ; BoronpH sensor

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Product Details of [ 87199-17-5 ]

CAS No. :87199-17-5 MDL No. :MFCD00151823
Formula : C7H7BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :VXWBQOJISHAKKM-UHFFFAOYSA-N
M.W : 149.94 Pubchem ID :591073
Synonyms :

Calculated chemistry of [ 87199-17-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.66
TPSA : 57.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.29
Log Po/w (WLOGP) : -0.82
Log Po/w (MLOGP) : -0.36
Log Po/w (SILICOS-IT) : -0.6
Consensus Log Po/w : -0.3

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.22
Solubility : 8.95 mg/ml ; 0.0597 mol/l
Class : Very soluble
Log S (Ali) : -1.06
Solubility : 13.1 mg/ml ; 0.087 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.22
Solubility : 9.08 mg/ml ; 0.0605 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.35

Safety of [ 87199-17-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P272-P273-P280-P302+P352-P333+P313-P362+P364-P501 UN#:N/A
Hazard Statements:H317-H401 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 87199-17-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 87199-17-5 ]

[ 87199-17-5 ] Synthesis Path-Downstream   1~101

  • 1
  • [ 14804-38-7 ]
  • [ 87199-17-5 ]
  • 4'-Methoxy-3',5'-dimethyl-biphenyl-4-carbaldehyde [ No CAS ]
  • 2
  • [ 455-13-0 ]
  • [ 87199-17-5 ]
  • [ 90035-34-0 ]
  • 3
  • [ 188290-36-0 ]
  • [ 87199-17-5 ]
  • [ 107834-03-7 ]
  • 4
  • [ 626-05-1 ]
  • [ 87199-17-5 ]
  • [ 588727-65-5 ]
YieldReaction ConditionsOperation in experiment
72% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70.0℃; for 12h;Inert atmosphere; 4-Formylphenylboronic acid (0.7 g, 4.64 mmol) was treated with 1 (1 g, 4.2 mmol) in THF:water (5:1) solvents mixture, Pd[PPh3]4 (0.24 g, 0.21 mmol), K2CO3 (1.72 g, 12.6 mmol) and stirred at 70 C for 12 h. The completion of the reaction was monitored by TLC. The mixture is extracted with DCM and dried over Na2SO4. The compound was purified by column chromatography (silica gel 60-120 mesh, hexane/EtOAc) (4:1 v/v) as an eluent to afford the compound 7 as a solid [29].
  • 5
  • [ 3032-81-3 ]
  • [ 87199-17-5 ]
  • [ 221018-04-8 ]
  • 6
  • [ 87199-17-5 ]
  • [ 173406-17-2 ]
  • 4'-formylbiphenyl-3-carboxylic acid t-butyl ester [ No CAS ]
  • 7
  • [ 51013-67-3 ]
  • [ 87199-17-5 ]
  • [ 13116-27-3 ]
  • 4'-biphenylmethyl-(4-morpholin-4-ylmethyl-phenyl)amine [ No CAS ]
  • 8
  • [ 87199-17-5 ]
  • [ 1779-58-4 ]
  • [ 13116-27-3 ]
  • [ 20883-99-2 ]
  • 9
  • [ 87199-17-5 ]
  • 2-pyrazinyl halide [ No CAS ]
  • [ 127406-08-0 ]
  • 10
  • [ 87199-17-5 ]
  • 3-pyridyl halide [ No CAS ]
  • [ 127406-55-7 ]
  • 12
  • [ 73096-42-1 ]
  • [ 87199-17-5 ]
  • [ 18039-42-4 ]
  • [ 151052-40-3 ]
  • 13
  • [ 615-59-8 ]
  • [ 87199-17-5 ]
  • 2'-methyl-[1,1';4',1'']terphenyl-4,4''-dicarbaldehyde [ No CAS ]
  • 14
  • [ 344-03-6 ]
  • [ 87199-17-5 ]
  • 2',3',5',6'-tetrafluoro-[1,1';4',1'']terphenyl-4,4''-dicarbaldehyde [ No CAS ]
  • 15
  • [ 87199-17-5 ]
  • [ 87441-19-8 ]
  • [ 862651-00-1 ]
  • 16
  • [ 87199-17-5 ]
  • [ 120173-41-3 ]
  • m,m'-bisformylphenyl-4-benzaldehyde [ No CAS ]
  • 17
  • [ 626-55-1 ]
  • [ 87199-17-5 ]
  • [ 127406-55-7 ]
YieldReaction ConditionsOperation in experiment
94% (a) 4-Pyridin-3-yl-benzaldehyde This aldehyde was prepared using the procedure for 4-pyridin-2-yl-benzaldehyde in Example 126 from 3-bromopyridine and 4-formylboronic acid to give a white crystalline solid (94%): mp=53-55 C.; Rf=0.08 (30% EtOAc/hexanes); IR (KBr) 1700, 1605, 1219 cm-1; 1H NMR (CDCl3) delta 7.55-7.60 (m, 1H), 7.76-7.79 (m, 2H), 8.01-8.05 (m, 2H), 8.08-8.12 (m, 1H), 8.69-8.71 (m, 1H), 8.94-8.95 (m, 1H), 10.10 (s, 1H). LRMS 184 (M+H).
87% With potassium phosphate tribasic heptahydrate; C18H24N3O2Pd; In ethanol; water; at 60℃; for 4h; General procedure: The reaction vessel was charged with heteroaryl bromides (1.0mmol), arylboronic acid (1.2mmol), K3PO4·7H2O (1.5mmol), and the catalyst 1 (0.5mol%) in EtOH/H2O (1:2, v/v 3mL). The reaction mixture was heated at 60C in air and the progress of the reaction was monitored by TLC. At the end of the reaction, the reaction mixture was diluted with water (20mL) and then extracted with EtOAc (2×20mL). The combined organic layers were washed with brine (10mL) and then dried over anhydrous Na2SO4. After removal of the solvent, the crude product was purified by flash chromatography over silica gel using ethyl acetate/hexane as an eluent to afford the pure product.
25% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 8h;Heating / reflux; Tetrakis (TRIPHENYLPHOSPHINE) palladium (0. 65 g, 0. 56 MMOL), 4-FORMYLPHENYLBORIC acid (2. 81 g, 18. 7 MMOL), 2M aqueous sodium carbonate (18. 7 ml, 37. 4 mmol) and ethanol were added to the nitrogen-saturated solution of 3-bromopyridine (2. 66 g, 16. 8 mmol) in toluene and refluxed under nitrogen for 8 hrs. Water was added to the solution and extracted with ethyl acetate, washed with water and brine and dried. Solvents were removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent ; hexane/ethyl acetate = 1/1. 5) to give 4- (3-PYRIDYL) benzaldehyde (0. 78 g, 25%).
  • 18
  • [ 153-78-6 ]
  • [ 87199-17-5 ]
  • 4-[(9H-fluoren-2-ylamino)methyl]phenylboronic acid [ No CAS ]
  • 19
  • [ 87199-17-5 ]
  • 3-pyridyl halide [ No CAS ]
  • [ 4385-62-0 ]
  • 20
  • [ 87199-17-5 ]
  • 3-pyridyl halide [ No CAS ]
  • [ 4385-76-6 ]
  • 21
  • [ 87199-17-5 ]
  • 3-pyridyl halide [ No CAS ]
  • [ 216959-91-0 ]
  • 23
  • [ 14508-49-7 ]
  • [ 87199-17-5 ]
  • [ 127406-08-0 ]
YieldReaction ConditionsOperation in experiment
97% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; for 18h;Heating / reflux; Step A Ethanol (13 ml) and 1.0M Na2CO3 (27.5 ml) were added to a suspension of 2-chloropyrazine (4.0 g, 34.6 mmole), 4-formylphenylboronic acid (6.8 g, 45.0 mmole), and tetrakis(triphenylphosphine)palladium(0) (2.0 g, 1.7 mmole) in toluene (55 ml). The mixture was refluxed for 18 hours then cooled, diluted with EtOAc, washed with NaHCO3, washed with brine, dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 4:1 hexanes/EtOAc) yielded 6.2 g (97%) of 4-(2-pyrazinyl)benzaldehyde.
42% [0410] Step A: [0411] 1M aq. Na2CO3 (20 mL) and ethanol (10 mL) were added to a solution of 2-chloropyrazine (2.30 g, 20.06 mmol), 4-formylphenylboronic acid (3.90 g, 26.01 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.60 g, 0.99 mmol) in toluene (40 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.56 g (42%) of 4-pyrazinylbenzaldehyde.
  • 24
  • [ 955959-84-9 ]
  • [ 87199-17-5 ]
  • [ 796071-07-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃; for 2 - 3h; A solution of dibenzofuran-4-boronic acid (1.0 g, 4.7 mmol) in ethanol (10 ML) was added to a stirred solution of 1- bromo-4-iodobenzene (1.33 g, 4.7 mmol) and tetrakis- (triphenylphosphine) palladium (0) (271 mg, 5 MOLpercent) in toluene (40 mL). 2N sodium carbonate (4.7 mL, 9.4 mmol) was added and the reaction was heated to 90°C (oil bath temp. ) for 2-3 hrs until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (2 x 20 mL). The combined extract was washed with water and brine. The ethereal solution was dried over anhydrous MGS04, filtered and concentrated in vacuo to yield 4- (4-BROMOPHENYL)-DIBENZOFURAN as a yellow solid, which was used immediately without further purification. A solution of 4-FORMYLPHENYLBORONIC acid (0.9 g, 5.64 mmol) in ethanol (10 mL) was added to a stirred solution of the crude 4- (4-BROMOPHENYL)-DIBENZOFURAN (from the previous reaction) in toluene (40 mL). tetrakis- (Triphenylphosphine) palladium (0) (270 mg, 5 molpercent) and 2N sodium carbonate (4.7 mL, 9.4 mmol) were added and the reaction was heated to 100°C (oil bath temp. ) for 2-3 hrs until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2 x 20 mL). The combined extract was washed with 0.5 N hydrochloric acid, water and brine and then dried over anhydrous MGS04, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 10-20percent ethyl acetate in hexane as eluent, afforded the title compound has a white solid (1.51g).
Example 7. 4' -Dibenzofuran-4-yl-biphenyl-4-carbaldehyde; EPO <DP n="91"/> A solution of dibenzofuran-4-boronic acid (1.0 g, 4.7 mmol) in ethanol (10 iriL) was added to a stirred solution of 1- bromo-4-iodobenzene (1.33 g, 4.7 mmol) and tetrakis- (triphenylphosphine)palladium(O) (271 mg, 5 molpercent) in toluene (40 mL) . 2N sodium carbonate (4.7 mL, 9.4 mmol) was added and the reaction was heated to 900C (oil bath temp.) for 2-3 hrs until complete (TLC control) .The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (2 x 20 mL) . The combined extract was washed with water and brine. The ethereal solution was dried over anhydrous MgSO4, filtered and concentrated in vacuo to yield 4- (4-bromophenyl) -dibenzofuran as a yellow solid, which was used immediately without further purification.A solution of 4-formylphenylboronic acid (0.9 g, 5.64 mmol) in ethanol (10 mL) was added to a stirred solution of the crude 4- (4-bromophenyl) -dibenzofuran (from the previous reaction) in toluene (40 mL) . tetrakis-(Triphenylphosphine)palladium(O) (270 mg, 5 molpercent) and 2N sodium carbonate (4.7 mL, 9.4 mmol) were added and the reaction was heated to 1000C (oil bath temp.) for 2-3 hrs until complete (TLC control) . The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2 x 20 mL) . The combined extract was washed with 0.5 N hydrochloric acid, water and brine and EPO <DP n="92"/>then dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 10-20percent ethyl acetate in hexane as eluent, afforded the title compound has a white solid (1.5Ig) .
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 100℃; for 2 - 3h; Example 1; 2-tert-Butoxycarbonylamino-3- (4 ' -dibenzofuran-4-yl-biphenyl-4- ylmethylsulfanyl) -propionic acid; Step 1; Preparation of 4' -Dibenzofuran-4~yl-biphenyl-4- carbaldehyde; A solution of dibenzofuran-4-boronic acid (1.0 g, 4.7 mmol) in ethanol (10 mL) was added to a stirred solution of 1- bromo-4-iodobenzene (1.33 g, 4.7 mmol) and tetrakis- (triphenylphosphine) -palladium(0) (271 mg, 5 molpercent) in toluene (40 mL) . 2 N sodium carbonate (4.7 mL, 9.4 mmol) was added and then the reaction was heated to 90 0C (oil bath temp.) for 2-3 h until complete (TLC control) . The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (2 x 20 mL) . The combined organic extracts were washed with water and sat'd aq NaCl. The ethereal solution was dried over anhyd MgSC>4, filtered and concentrated in vacuo to yield 4- (4-bromophenyl) - dibenzofuran as a yellow solid, which was used immediately without further purification.A solution of 4-formylphenylboronic acid (0.9 g, 5.64 mmol) in ethanol (10 mL) was added to a stirred solution of the crude 4- (4-bromophenyl) -dibenzofuran (from the previous EPO <DP n="111"/>reaction) in toluene (40 mL) . Tetrakis- (Triphenylphosphine) - palladium(0) (270 mg, 5 molpercent) and 2 N sodium carbonate (4.7 mL, 9.4 mmol) were added and then the reaction was heated to 100 0C (oil bath temp.) for 2-3 h until complete (TLC control) . The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2 x 20 mL) . The combined organic extracts were washed with 0.5 N hydrochloric acid, water and sat'd aq NaCl and then dried over anhyd MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (10-20percent ethyl acetate in heptane) afforded the title compound has a white solid (1.5Ig) .
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃; for 2 - 3h; A solution of dibenzofuran-4-boronic acid (1.0 g, 4.7 mmol) in ethanol (10 ML) was added to a stirred solution of 1- bromo-4-iodobenzene (1.33 g, 4.7 mmol) and tetrakis- (TRIPHENYLPHOSPHINE)-PALLADIUM (O) (271 mg, 5 molpercent) in toluene (40 mL). 2 N sodium carbonate (4.7 mL, 9.4 mmol) was added and then the reaction was heated to 90 °C (oil bath temp. ) for 2-3 h until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (2 x 20 mL). The combined organic extracts were washed with water and sat'd aq NaCl. The ethereal solution was dried over anhyd MGS04, filtered and concentrated in vacuo to yield 4- (4-BROMOPHENYL)- dibenzofuran as a yellow solid, which was used immediately without further purification. A solution of 4-formylphenylboronic acid (0.9 g, 5.64 mmol) in ethanol (10 ML) was added to a stirred solution of the crude 4- (4-BROMOPHENYL)-DIBENZOFURAN (from the previous reaction) in toluene (40 mL). TETRAKIS- (TRIPHENYLPHOSPHINE)- palladium (0) (270 mg, 5 molpercent) and 2 N sodium carbonate (4.7 mL, 9.4 mmol) were added and then the reaction was heated to 100 °C (oil bath temp. ) for 2-3 h until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2 x 20 mL). The combined organic extracts were washed with 0.5 N hydrochloric acid, water and sat'd aq NaCl and then dried over anhyd MGS04, filtered and concentrated in vacuo. Purification by flash column chromatography (10-20percent ethyl acetate in heptane) afforded the title compound has a white solid (1.51g).

  • 25
  • [ 402-43-7 ]
  • [ 87199-17-5 ]
  • [ 90035-34-0 ]
YieldReaction ConditionsOperation in experiment
12.1 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 85℃; for 2h; Reference Example 6-2 4'-(Trifluoromethyl)biphenyl-4-carbaldehyde A mixture of 4-bromobenazotrifluoride (10.0 g), 4-formylphenylboronic acid (7.33 g), tetrakis(triphenylphosphine)palladium(0) (308 mg), potassium carbonate (30.7 g), tetrahydrofuran (300 mL) and water (100 mL) was stirred at 85C for 2 hours. After cooling the reaction mixture to room temperature, water was added to it, which was then extracted with ethyl acetate twice and the combined organic layers were washed with saturated brine. After adding anhydrous magnesium sulfate to the organic layers, the desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in n-hexane (60 mL) with heating and thereafter cooled to 0C. The resulting precipitate was recovered by filtration to give the titled compound as a gray solid (12.1 g). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 7.71 - 7.80 (m, 6 H) 7.96 - 8.03 (m, 2 H) 10.09 (s, 1 H). MS EI posi: 250[M]+.
  • 26
  • [ 1120-95-2 ]
  • [ 87199-17-5 ]
  • 4-[Pyridazin-3-yl]-Benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; for 20h;Heating / reflux; Step B Ethanol (10 ml) and 1.0M Na2CO3 (18 ml) were added to a suspension of the compound from step A (2.8 g, 24.0 mmole), 4-formylphenylboronic acid (4.7 g, 31.2 mmole), and tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmole0 in toluene (35 ml). The mixture was refluxed for 20 hours then cooled, diluted with EtOAc, washed with NaHCO3, washed with brine, dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 4:1 hexanes/EtOAc) yielded 4.1 g (93percent) of 4-(3-pyridazinyl)benzaldehyde.
  • 27
  • [ 3034-53-5 ]
  • [ 87199-17-5 ]
  • [ 198904-53-9 ]
YieldReaction ConditionsOperation in experiment
95% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 115℃; for 24h;Inert atmosphere; The (4-formylphenyl)boronic acid 118 (0.30 g, 2.0 mmol), 2-bromo-l,3-thiazole 119a (0.33 g, 2.0 mmol), Pd(PPh3)4(0.12 g, 0.1 mmol), aqueous solution of potassium carbonate (0.4 M, 5 mL), ethanol (5 mL) and toluene (2mL) were added to a 50 mL flask under nitrogen. The reaction mixture was stirred at 115 C for 24 hours and then cooled to room temperature. After removing the solvent, the crude residue was purified by column chromatography on silica gel using EA/hexane (1/5) as eluent. The product 120a was obtained as a white solid at a yield of 95%.
74% With sodium carbonate;tetrakis(triphenylphosphine)palladium (0); In ethanol; water; toluene; (1) A mixture of 2-bromothiazole (0.9 ml, 10 mmols), 4-formylphenylboronic acid (1.65 g, 11 mmols), sodium carbonate (2.65 g, 25 mmols), toluene (150 ml), ethanol (30 ml) and water (30 ml) was stirred in an argon atmosphere at room temperature for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.58 mg, 0.5 mmols) was added thereto and heated under reflux for 15 hours. The reaction mixture was cooled, poured into water, and extracted with ethyl acetate. The extract was washed with water and brine, then dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography, and then recrystallized from ethyl acetate/hexane to give 4-(2-thiazolyl)benzaldehyde (1.4 g, 74 %).m.p. 91.5-92.5C Elemental Analysis for C10H7NOS: Calcd.: C, 63.47; H, 3.73; N, 7.40 Found: C, 63.67; H, 3.60; N, 7.316 1H-NMR (CDCl3) delta: 7.46(1H,d,J=3.2Hz), 7.95-7.99(3H,m),
998 mg (35%) With sodium hydrogencarbonate;tetrakis(triphenylphosphine)palladium (0); In 1,2-dimethoxyethane; water; REFERENCE EXAMPLE 72 4-(2-Thiazolyl)benzaldehyde A mixture of NaHCO3 (3.83 g, 45.6 mmol) and 4-formylphenylboronic acid (2.69 g, 18.0 mmol) in water (60 mL) was added to a solution of 2-bromothiazole (2.50 g, 15.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (500 mg, 0.43 mmol) in DME (60 mL). The reaction mixture was heated to reflux for 18 h, cooled to room temperature, diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried with Na2SO4, and concentrated in vacuo. Two consecutive recrystallizations from hexanes/ethyl acetate yielded 998 mg (35%) of the title compound. MS 190 (M+H)+.
985 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 20℃;Inert atmosphere; Reflux; (1) 4-(thiazol-2-yl)benzaldehyde 2-Bromothiazole (0.538 ml, 6.06 mmol), 4-formylphenylboronic acid (1.0 g, 6.67 mmol), and Na2CO3 (1.61 g) were suspended in the mixed solution of toluene (25 ml), ethanol (5 ml), and H2O (5 ml). The mixture was stirred at room temperature for 15 minutes under an argon gas atmosphere. After reducing the pressure inside of the reaction container by using a vacuum line, the mixture was degassed by introducing Ar gas and this procedure was repeated twice. After that, tetrakis(triphenylphosphine)palladium (0.701 g, 0.606 mmol) was added, and the mixture was stirred for 15 hours by heating under reflux. The end point of the reaction was confirmed on TLC (EtOAc:n-hexane=1:4), and the mixture was cooled to room temperature. H2O (50 ml) and EtOAc (50 ml) were added and the mixture was stirred for 15 minutes. Black insoluble matter was removed by filtration with Celite and the filtrate was separated by the step of extraction/separation. The organic layer was washed with saturated brine (50 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified on silica gel column chromatography (EtOAc:hexane=1:3) to obtain the title compound (985 mg) as an opaque white solid.

  • 28
  • [ 475160-93-1 ]
  • [ 87199-17-5 ]
  • [ 224311-51-7 ]
  • [ 475160-94-2 ]
YieldReaction ConditionsOperation in experiment
63% With KF;palladium diacetate; In tetrahydrofuran; (4'-Formylbiphenyl-2-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S29). 4-Formylphenylboronic acid (4.97 g, 33.2 mmol), aryl bromide S28 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.884 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated moderately (30° C.) with stirring. After 24 h, the reaction was diluted with CH2Cl2 and was washed with 1 M NaOH. The aqueous layer was extracted with CH2Cl2 and the combined organics were then washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude solid was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain a white solid (6.0 g, 63percent). 1H NMR (400 MHz, d6-DMSO): delta10.04 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.88 (d, 2H, J=7.5 Hz), 7.82 (t, 1H, J=5.9 Hz, NH), 7.67 (d, 2H, J=7.5 Hz), 7.59 (d, 2H, J=8.2 Hz), 7.43-7.30 (m, 7H), 7.24 (d, 1H, J=7.7 Hz), 4.29 (d, 2H, J=7.0 Hz), 4.19 (t, 1H, J=7.0 Hz), 4.12 (d, 2H, J=5.9 Hz). APCI/MS: 434 (M+H+).
63% With KF;palladium diacetate; In tetrahydrofuran; (4'-Formylbiphenyl-2-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S29). 4-Formylphenylboronic acid (4.97 g, 33.2 mmol), aryl bromide S28 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.884 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated moderately (30° C.) with stirring. After 24 h, the reaction was diluted with CH2Cl2 and was washed with 1 M NaOH. The aqueous layer was extracted with CH2Cl2 and the combined organics were then washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude solid was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain a white solid (6.0 g, 63percent). 1H NMR (400 MHz, d6-DMSO): delta10.04 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.88 (d, 2H, J=7.5 Hz), 7.82 (t, 1H, J=5.9 Hz, NH), 7.67 (d, 2H, J=7.5 Hz), 7.59 (d, 2H, J=8.2 Hz), 7.43-7.30 (m, 7H), 7.24 (d, 1H, J=7.7 Hz), 4.29 (d, 2H, J=7.0 Hz), 4.19 (t, 1H, J=7.0 Hz), 4.12 (d, 2H, J=5.9 Hz). APCI/MS: 434 (M+H+).
  • 29
  • [ 87199-17-5 ]
  • [ 224311-51-7 ]
  • [ 475160-92-0 ]
  • [ 475160-95-3 ]
  • [ 475160-94-2 ]
YieldReaction ConditionsOperation in experiment
60% With KF;palladium diacetate; In tetrahydrofuran; (4'-Formylbiphenyl-3-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S30). 4-Formylphenylboronic acid (5.0 g, 33 mmol), aryl bromide S27 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.88 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated to reflux with stirring. After 5 h, the reaction was diluted with ethyl acetate, filtered through a celite pad and washed with 1 M NaOH. The aqueous layer was extracted with ethyl acetate and the combined organics were then washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford an orange oil (13 g). The crude oil was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain aldehyde S29 as a yellow oil (5.7 g, 60percent). 1H NMR (400 MHz, CDCl3): delta10.06 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.76 (d, 2H, J=7.5 Hz), 7.74 (d, 2H, J=8.2 Hz), 7.59 (d, 2H, J=7.5 Hz), 7.56 (m, 1H), 7.55 (s, 1H), 7.46 (dd, 1H, J=7.9 Hz, 7.9 Hz), 7.39 (dd, 2H, J=7.5 Hz, 7.5 Hz), 7.33 (m, 1H), 7.29 (dd, 2H, J=7.5 Hz, 7.5 Hz), 5.16 (broad s, 1H), 4.48 (d, 2H, J=7.0 Hz), 4.47 (s, 2H), 4.24 (t, 1H, J=7.0 Hz). ESI/MS: 456 (M+Na+).
60% With KF;palladium diacetate; In tetrahydrofuran; (4'-Formylbiphenyl-3-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S30). 4-Formylphenylboronic acid (5.0 g, 33 mmol), aryl bromide S27 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.88 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated to reflux with stirring. After 5 h, the reaction was diluted with ethyl acetate, filtered through a celite pad and washed with 1 M NaOH. The aqueous layer was extracted with ethyl acetate and the combined organics were then washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford an orange oil (13 g). The crude oil was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain aldehyde S29 as a yellow oil (5.7 g, 60percent). 1H NMR (400 MHz, CDCl3): delta10.06 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.76 (d, 2H, J=7.5 Hz), 7.74 (d, 2H, J=8.2 Hz), 7.59 (d, 2H, J=7.5 Hz), 7.56 (m, 1H), 7.55 (s, 1H), 7.46 (dd, 1H, J=7.9 Hz, 7.9 Hz), 7.39 (dd, 2H, J=7.5 Hz, 7.5 Hz), 7.33 (m, 1H), 7.29 (dd, 2H, J=7.5 Hz, 7.5 Hz), 5.16 (broad s, 1H), 4.48 (d, 2H, J=7.0 Hz), 4.47 (s, 2H), 4.24 (t, 1H, J=7.0 Hz). ESI/MS: 456 (M+Na+).
  • 30
  • [ 22536-63-6 ]
  • aq. Na2CO3 [ No CAS ]
  • PdCl2(1,4-bis(diphenylphosphino)butane) [ No CAS ]
  • [ 87199-17-5 ]
  • 4-(4-methoxy-2-pyrimidinyl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.80 g (42%) In ethanol; toluene; REFERENCE EXAMPLE 13 4-(4-Methoxy-2-pyrimidinyl)benzaldehyde 1M aq. Na2CO3 (20 mL) and ethanol (10 mL) were added to a solution of <strong>[22536-63-6]<strong>[22536-63-6]2-chloro-4-methoxypyrimidin</strong>e</strong> (2.90 g, 20.06 mmol, prepared as described in Tetrahedron 1997, 53, 11595), 4-formylphenylboronic acid (3.90 g, 26.01 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.60 g, 0.99 mmol) in toluene (40 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.80 g (42%) of the title compound. MS 215 (M+H)+.
1.80 g (42%) In ethanol; toluene; Reference Example 13 4-(4-methoxy-2-pyrimidinyl)benzaldehyde 1 M aq. Na2CO3 (20 mL) and ethanol (10 mL) were added to a solution of <strong>[22536-63-6]<strong>[22536-63-6]2-chloro-4-methoxypyrimidin</strong>e</strong> (2.90 g, 20.06 mmol, prepared as described in Tetrahedron 1997, 53, 11595), 4-formylphenylboronic acid (3.90 g, 26.01 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.60 g, 0.99 mmol) in toluene (40 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.80 g (42%) of the title compound. MS 215 (M+H)+.
  • 31
  • [ 10386-27-3 ]
  • [ 87199-17-5 ]
  • 2-(4-formylphenyl)isonicotinonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With cesium fluoride;tetrakis(triphenylphosphine)palladium (0); In 2-Methyl-1,2-propanediol; Preparation 72 2-(4-formylphenyl)-4-pyridyl cyanide Benzaldehyde-4-boronic acid (1.36 g), 2-bromo-4-cyano pyridine (1.5 g), cesium fluoride (2.72 g) and tetrakis(triphenylphosphine)palladium(0) (285 mg) were mixed together in dimethyl ethylene glycol (30 ml). The reaction mixture was refluxed for 16 hrs under a atmosphere of nitrogen after which time the cooled mixture was diluted with diethyl ether (40 ml) and washed with water (40 ml), the organic layer was separated and washed with saturated brine, dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by column chromatography eluding with Dichloromethane/Diethyl ether (97.5/2.5, v/v) to afford the title compound (0.81 g). Rf 0.3 (Dichloromethane/Diethyl ether, 97.5/2.5, v/v). deltaH (400 MHz, CDCl3): 10.15 (1H, s), 8.95 (1H, d), 8.20 (2H, d), 8.05 (3H, m), 7.55 (1H, d).
  • 32
  • [ 33543-78-1 ]
  • [ 87199-17-5 ]
  • [ 920511-27-9 ]
YieldReaction ConditionsOperation in experiment
With oxygen;di-mu-hydroxo-bis[(N,N,N?,N?-tetramethylethylene-diamine)copper(II)] chloride; In 1,2-dichloro-ethane; at 60℃; for 20h; Description 45; Ethyl 1-(4-formylphenyl)-1H-imidazole-2-carboxylate (D45); <strong>[33543-78-1]Ethyl imidazole-2-carboxylate</strong> (140 mg, 1.0 mmol), 4-formylbenzeneboronic acid (300 mg, 2.0 mmol) and catalyst [Copper(OH).TMEDA]2Cl2 (46 mg, 0.10 mmol) were dissolved in 1,2-dichloroethane (5 ml) and heated to 60° C. under an O2 atmosphere for 20 h. The mixture was diluted with DCM, filtered through Celite and evaporated to dryness. The crude residue was purified by column chromatography on silica, eluting with a 0-5percent [2M NH3 in MeOH]/DCM gradient to give the title compound (152 mg). deltaH (CDCl3, 250 MHz) 1.32 (3H, t), 4.32 (2H, q), 7.22 (1H, s), 7.34 (1H, s), 7.52 (2H, d), 8.01 (2H, d), 10.11 (1H, s). MS (ES): MH+ 245.
With oxygen;di-mu-hydroxo-bis[(N,N,N?,N?-tetramethylethylene-diamine)copper(II)] chloride; In 1,2-dichloro-ethane; at 60℃; for 20h; Description 45; Ethyl 1-(4-formylphenyl)-1H-imidazole-2-carboxylate (D45); <strong>[33543-78-1]Ethyl imidazole-2-carboxylate</strong> (140mg, 1. Ommol), 4-formylbenzeneboronic acid (300mg, 2.0mmo.) and catalyst [Copper(OH).TMEDA] 2CI2 (46mg, 0.1 Ommol) were dissolved in 1 ,2-dichloroethane (5ml) and heated to 60°C under an O2 atmosphere for 2Oh. The mixture was diluted with DCM, filtered through Celite and evaporated to dryness. The crude residue was purified by column chromatography on silica, eluting with a 0-5percent [2M NH3 in MeOH]/DCM gradient to give the title compound (152mg). deltaH (CDCI3, 250MHz) 1.32 (3H, t), 4.32 (2H, q), 7.22 (1 H, s), 7.34 (1H, s), 7.52 (2H, d), 8.01 (2H, d), 10.11 (1H, s). MS (ES): MH+ 245.
  • 33
  • [ 40032-73-3 ]
  • [ 87199-17-5 ]
  • [ 1019780-54-1 ]
  • 34
  • [ 889939-26-8 ]
  • [ 87199-17-5 ]
  • [ 942921-71-3 ]
YieldReaction ConditionsOperation in experiment
45% With sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride; In 1,4-dioxane; water; at 95℃; for 3h; Procedure 2:Step A : 4-[4-bromo-1 -(phenylsulfonyl)-i H-pyrrolo[2,3-6]pyridin-2 yl]benzaldehyde; In a microwave reaction vial was placed 4-bromo-2-iodo-1-(phenylsulfonyl)-1 H- pyrrolo[2,3-6]pyridine (5 g, 10.80 mmol), which was prepared according to WO2003000690 with a minor modification by replacing para-toluenesulfonyl chloride by benzenesulfonyl chloride, (4-formyl phenyl )boronic acid (1.62 g, 10.80 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (1.34 g, 1.62 mmol) and sodium <n="44"/>bicarbonate (1.81 g, 21.60 mmol). Then dioxane (32 mL) and water (11 ml.) were added and the vial was sealed and then three cycles of high vac/nitrogen were performed and the reaction mixture was heated at 95 0C for 3 h. After cooling to room temperature the reaction mixture was filtered through celite and washed with methanol. Silica was added and the volatiles were evaporated under reduced pressure and the residue was purified by flash chromatography (5% to 60%) ethyl acetate: hexanes to afford 2.16 g (45%) of the title compound. 1H NMR (400 MHz, DMSOd6) delta 10.12 (s, 1 H) 8.28 (d, J = 5.1 Hz, 1 H) 8.04 (d, J = 8.1 Hz, 2 H) 7.86 (dd, J = 10.4, 7.9 Hz, 4 H) 7.69 (t, J = 7.5 Hz, 1 H) 7.64 (d, J = 5.5 Hz, 1 H) 7.57 (t, J = 7.9 Hz, 2 H) 6.95 (s, 1 H), MS (ESI): 442 [M+H]+.
  • 35
  • [ 30483-75-1 ]
  • [ 87199-17-5 ]
  • [ 893739-03-2 ]
  • 36
  • [ 22536-67-0 ]
  • [ 87199-17-5 ]
  • [ 932405-46-4 ]
YieldReaction ConditionsOperation in experiment
Catalyze; Example 42Preparation of 4-[2-(4-trifluoromethoxyphenyl)-pyrimidin-5-yl]-benzaldehyde Step 1. 4-(2-Chloropyrimidin-5-yl)-benzaldehyde. The compound was prepared by palladium-catalyzed arylation of <strong>[22536-67-0]2,5-dichloropyrimidine</strong> and 4-formylphenyl boronic acid.
  • 37
  • [ 30314-45-5 ]
  • [ 87199-17-5 ]
  • [ 1221402-02-3 ]
  • 38
  • [ 1008360-84-6 ]
  • [ 87199-17-5 ]
  • [ 76-83-5 ]
  • [ 1008360-87-9 ]
  • [ 1008360-88-0 ]
YieldReaction ConditionsOperation in experiment
To a solution of 5-bromo-6-fluoro-1-(triphenylmethyl)-1H-benzimidazole and 6-bromo-5-fluoro-1-(triphenylmethyl)-1H-benzimidazole (2.0 g, 4.4 mmol) in toluene (10 mL) under nitrogen atmosphere was added tetrakis(triphenylphosphine) palladium(0) (0.25 g, 0.2 mmol) followed by a solution of sodium bicarbonate (0.92 g, 11.0 mmol) in water (5 mL). A solution of 4-formylphenylboronic acid (0.72 g, 4.8 mmol) in ethanol (3 mL) was then added and the reaction was heated at reflux overnight. After removal of the solvent in vacuo, the residue was partitioned between ethyl acetate and water. The combined organics were dried over sodium sulfate, concentrated in vacuo, and purified via chromatography (20 to 50% ethyl acetate/hexanes) to provide the product as a mixture of trityl regioisomers, 4-[5-fluoro-1-(triphenylmethyl)-1H-benzimidazol-6-yl]benzaldehyde and 4-[6-fluoro-1-(triphenylmethyl)-1H-benzimidazol-5-yl]benzaldehyde.Isomer a: 1H NMR (400 MHz, CDCl3) delta 6.45-6.48 (m, 1H), 7.16-7.26 (m, 8H), 7.35-7.39 (m, 9H), 7.65-7.72 (m, 1H), 7.81 (d, J=7.4 Hz, 1H), 8.12-8.22 (m, 1H), 9.99 (s, 1H).Isomer b: 1H NMR (400 MHz, CDCl3) delta 6.27 (d, J=11.2 Hz, 1H), 7.17-7.21 (m, 6H), 7.34-7.37 (m, 9H), 7.70 (d, J=6.6 Hz, 2H), 7.85 (d, J=7.1 Hz, 1H), 7.92-7.96 (m, 3H), 10.04 (s, 1H).
  • 39
  • [ 87199-17-5 ]
  • [ 34259-99-9 ]
  • [ 127406-12-6 ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 16h;Reflux; Inert atmosphere; To a solution of <strong>[34259-99-9]<strong>[34259-99-9]4-bromothiazol</strong>e</strong> (see The Journal of Organic Chemistry, 71, 3754 (2006)) (1.31 g, 7.98 mmol) in 1,2-dimethoxyethane (38.0 ml) were added 4-formylphenylboronic acid (1.45 g, 9.67 mmol), sodium hydrogencarbonate (2.00 g, 23.8 mmol) and water (19 ml), which was deaerated under reduced pressure, followed by argon substitution. Tetrakis(triphenylphosphine)palladium (270 mg, 0.234 mmol) was then added, followed by heating to reflux for 16 hours under argon atmosphere. After completion of the reaction, a saturated aqueous sodium chloride solution was added to the reaction solution, followed by extraction with chloroform. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=4:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.29 g) as a slightly yellow solid. (Yield: 85percent) Mass spectrum (CI, m/z): 190 (M++1). 1H-NMR spectrum (CDCl3, ppm): 10.05 (s, 1H), 8.93 (d, J=2.0Hz, 1H), 8.14-8.10 (m, 2H), 799-7.94 (m, 2H), 7.73 (d, J=2.0Hz, 1H).
85% With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 16h;Inert atmosphere; Reflux; 15-(a) 4-(Thiazol-4-yl)benzaldehyde To a solution of <strong>[34259-99-9]<strong>[34259-99-9]4-bromothiazol</strong>e</strong> (see The Journal of Organic Chemistry, 71, 3754 (2006)) (1.31 g, 7.98 mmol) in 1,2-dimethoxyethane (38.0 ml) were added 4-formylphenylboronic acid (1.45 g, 9.67 mmol), sodium hydrogencarbonate (2.00 g, 23.8 mmol) and water (19 ml), which was deaerated under reduced pressure, followed by argon substitution. Tetrakis(triphenylphosphine)palladium (270 mg, 0.234 mmol) was then added, followed by heating to reflux for 16 hours under argon atmosphere. After completion of the reaction, a saturated aqueous sodium chloride solution was added to the reaction solution, followed by extraction with chloroform. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=4:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.29 g) as a slightly yellow solid. (Yield: 85percent) Mass spectrum (CI, m/z): 190 (M++1). 1H-NMR spectrum (CDCl3, deltappm): 10.05 (s, 1H), 8.93 (d, J=2.0Hz, 1H), 8.14-8.10 (m, 2H), 7.99-7.94 (m, 2H), 7.73 (d, J=2.0Hz, 1H).
  • 41
  • [ 20157-44-2 ]
  • [ 87199-17-5 ]
  • [ 1269926-04-6 ]
  • 42
  • [ 22536-67-0 ]
  • [ 87199-17-5 ]
  • [ 1261551-78-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In ethanol; toluene; at 60℃; for 1.5h;Inert atmosphere; Palladium dichloro-bis(triphenylphosphine) (3.5 g) was added to a stirred solution of 4-formylbenzene boronic acid (32.5 g), <strong>[22536-67-0]2,5-dichloro-pyrimidine</strong> (30 g) in toluene (1000 ml) and ethanol (100 ml) under an argon atmosphere. The solution was purged with argon and aqueous sodium carbonate (2N) (200 ml) was added. The reaction mixture was stirred at 600C for 90 minutes, cooled to ambient temperature, diluted with ethyl acetate, and washed successively with aqueous sodium hydrogen carbonate (saturated), water and brine. The combined organic extracts were treated with charcoal, dried over sodium sulfate, filtered through Hyflo and concentrated in vacuo. The residue was triturated with diethyl ether (100 ml), the solid isolated by filtration and dried under high vacuum to give 4-(5-chloro- pyrimidin-2-yl)-benzaldehyde as a white solid. M.p. 186C. IH NMR (400 MHz, DMSO) 8.10 (d, 2H), 8.55 (d, 2H), 9.1 (s, 2H).
  • 43
  • [ 1120-90-7 ]
  • [ 87199-17-5 ]
  • [ 127406-55-7 ]
  • 44
  • [ 87199-17-5 ]
  • [ 474918-32-6 ]
  • [ 1334287-59-0 ]
YieldReaction ConditionsOperation in experiment
70% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; toluene; at 90℃;Inert atmosphere; Compound 4-formyl phenylboronic acid (300 mg, 0 . 76mmol), 2-bromo -9,9 the base fluorene-diethyl [...] (103 mg, 0 . 67mmol), double (triphenylporphyrin phosphorus) palladium dichloride Pd (PPh3)2Cl2(23.51 mg, 0 . 034mmol), dissolved in 10 ml tetrahydrofuran mixed solvent of toluene and (Vtoluene: VTHF= 1:1) in, under the protection of nitrogen 90 C reflux reaction, thin-layer chromatography tracking to the reaction is complete. The solution obtained after the organic solvent, a revolving off, the extraction with ethyl acetate, the organic layer three times washing with water, saturated NaCl solution to a washing, drying by anhydrous sodium sulfate, reducing pressure and evaporating the solvent. The crude product using petroleum ether and ethyl acetate mixed solvent (20:1) column, to obtain 4 - (9,9 the [...] -diphenyl -9H-fluoren-2-yl) benzaldehyde (white solid, 251.1 mg, yield 70%).
  • 45
  • [ 87199-17-5 ]
  • [ 474918-32-6 ]
  • 7-[4-(9,9-diphenyl-9H-fluoren-2-yl)styryl]-9,9-diethyl-2-(N,N-diphenylamino)-9H-fluorene [ No CAS ]
  • 46
  • [ 3437-95-4 ]
  • [ 87199-17-5 ]
  • [ 107834-03-7 ]
  • 47
  • [ 36193-65-4 ]
  • [ 87199-17-5 ]
  • [ 1374451-92-9 ]
YieldReaction ConditionsOperation in experiment
A mixture of 1.0 g (7.04 mmol) of lH-<strong>[36193-65-4]indole-2-carbonitrile</strong> (I. Borza at al.Bioorg. Med. Chem. Lett. 2005, 15, 5439-5441), 1.5 g (7.28 mmol) of trimethyltin azide, and 50 mL of toluene was refluxed for 3 h. The reaction mixture was cooled to 20 C and the precipitated product was filtered off to yield 2.22 g of tin complex of the title compound. Mp.: 236-240 C. A mixture of 0.4 g (1.4 mmol) of 2-(2H-tetrazol-5-yl)-lH-indole, 0.31 g (2.06 mmol) of 4-formyl-phenylboronic acid, 0.42 g (2.77 mmol) of copper(II) acetate, 0.98 mL (5.6 mmol) of N^V-diisopropylethylamine, 0.7 g 3 A molecular sieves in 15 mL of N,N-dimethylformamide was vigorously stirred at room temperature with air bubbling for 14 h. The mixture was filtered through Celite. The filtrate was concentrated in vacuo. The residue was submitted to flash column chromatography using Kieselgel 60 (0.015-0.040 mm) as adsorbent (Merck) and chloroform:methanol:acetic acid = 10: 1 :0.1 as eluent to yield after crystallization from 2-propanol 0.12 g (19 %) of the title compound. Mp.: 210-212 C.
  • 48
  • [ 87199-17-5 ]
  • [ 292638-85-8 ]
  • [ 7560-50-1 ]
  • 49
  • [ 18648-66-3 ]
  • [ 87199-17-5 ]
  • [ 217449-95-1 ]
  • 50
  • [ 1403257-80-6 ]
  • [ 87199-17-5 ]
  • [ 1403258-06-9 ]
YieldReaction ConditionsOperation in experiment
66% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 2h;Inert atmosphere; Step 3: Synthesis of N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-5-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-4'-formyl-4-methyl-[1,1'-biphenyl]-3-carboxamide To a stirred solution of <strong>[1403257-80-6]5-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzamide</strong> (5.0 g, 10 mmol) and (4-formylphenyl)boronic acid (2.35 g, 15.8 mmol) in dioxane/water (30 mL/10 mL) was added Na2CO3 (4.01 g, 37.9 mmol). The solution was purged with argon for 15 min., Pd(PPh3)4 (1.21 g, 1.05 mmol) and the mixture was heated at 100 C. for 2 h. The mixture was allowed to cool to room temperature, diluted with water and extracted with 10% MeOH/CH2Cl2. The combined organic layers were dried over sodium sulphate and the solvent removed under reduced pressure. The resulting crude material was purified by column chromatography over silica gel to afford N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-5-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-4'-formyl-4-methyl-[1,1'-biphenyl]-3-carboxamide (3.5 g, 66%).
  • 52
  • [ 96-43-5 ]
  • [ 87199-17-5 ]
  • [ 107834-03-7 ]
YieldReaction ConditionsOperation in experiment
87% With C27H39Br2N3Pd; potassium hydroxide; In isopropyl alcohol; at 82℃; for 0.166667h; General procedure: A two-necked 25.0mL flask fitted with a reflux condenser and septum was charged with aryl halide (1.0mmol), phenylboronic acid (1.2mmol), KOH (2.0mmol), diethyleneglycol-di-n-butylether (0.6mmol, internal standard), and the palladium-pyridine catalyst (0.01mol %) in isopropyl alcohol (1.0mL) was added. The mixture was heated to 82C under an air atmosphere. The conversion was monitored by gas chromatography.
  • 53
  • [ 19393-92-1 ]
  • [ 87199-17-5 ]
  • [ 1181237-88-6 ]
  • 54
  • [ 877264-77-2 ]
  • [ 87199-17-5 ]
  • [ 1301189-02-5 ]
YieldReaction ConditionsOperation in experiment
33% With water; caesium carbonate;tetrakis(triphenylphosphine) palladium(0); at 100℃; A mixture of 1 , 1 -dimethylethyl 6-bromo-lH-indazole-l-carboxylate (0.675 mmol), (4-formylphenyl)boronic acid (0.675 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.034 mmol), in 2M aq cesium carbonate (2 mL) and 1 ,4-dioxane (10 mL) was heated at 100 °C overnight. The reaction mixture was concentrated in vacuo and the residue purified by preparative TLC to afford the title product as a solid (33percent).
  • 55
  • [ 474688-76-1 ]
  • [ 87199-17-5 ]
  • (4-(10-(naphthalen-2-yl)-9-(naphthalen-3-yl)anthracen-7-yl))benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
47.6% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; for 72h;Reflux; (Preparation of a compound represented by Chemical Formula 1-4) The compound of Chemical Formula i prepared in Preparation Example 9 (4.00 g, 7.85 mmol) and 4-formylphenylboronic acid (3.53 g, 23.5 mmol) were introduced into a solution of 20 mL of 2 N potassium carbonate solution and 60 mL of toluene, Pd(PPh3)4 (0.27 g, 0.23 mmol) was added while stirring, and the mixture was refluxed for 3 days. The organic layer was separated, washed with water, dried over magnesium sulfate, and passed through a silica gel layer, and concentrated to obtain a solid compound. The solid was dispersed in 100 mL of ethanol, filtered, and recrystallized from ethyl acetate to obtain anthracene phenylaldehyde (2.00 g, 47.6%).
  • 56
  • [ 474688-76-1 ]
  • [ 87199-17-5 ]
  • 2-(4-(9,10-bis(naphthalen-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzimidazole [ No CAS ]
  • 57
  • [ 87199-17-5 ]
  • [ 198904-31-3 ]
  • 58
  • [ 17933-03-8 ]
  • [ 87199-17-5 ]
  • [ 400744-83-4 ]
YieldReaction ConditionsOperation in experiment
85% General procedure: Arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0mg) were added to a 20 mL Schlenk-tube equipped with amagnetic stir bar. The tube was evacuated twice and backfilledwith N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg)were added to the tube at r.t. under a stream of N2, and thetube was sealed and placed into a pre-heated oil bath at 80 Cfor 8-12 h. The resulting solution was cooled to r.t., and thenarylboronic acid 1? (0.75 mmol) and Pd(OAc)2 (0.025 mmol, 5.6 mg) were added, and the mixture stirred at 80 C for 12-16 h. The resulting solution was cooled to r.t. and H2O (10mL) was added. The aq layer was extracted with EtOAc(3 × 5 mL). The combined organic phase was dried overanhydrous Na2SO4, filtered and concentrated by rotaryevaporation, and the residue was purified by columnchromatography on silica gel to provide the desired product3a-v. Data for three representative examples are provided
  • 59
  • [ 87199-17-5 ]
  • [ 138500-88-6 ]
  • 60
  • [ 2050-47-7 ]
  • [ 87199-17-5 ]
  • [ 1622332-58-4 ]
YieldReaction ConditionsOperation in experiment
16% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In monoethylene glycol diethyl ether; water; at 110℃; for 24h;Inert atmosphere; 4-Formylphenylboronic acid (2.73 g, 18.3 mmol), bis-(4-bromophenyl)ether (3.01 g, 9.15 mmol), Pd(PPh3)4 (170 mg, 0.15 mmol)and a potassium carbonate solution (8.01 g, 58.0 mmol) in water(20 mL) were dissolved in 1,2-dimethoxyethane (200 mL). The mixture was heated at 110C for 24 h under an Ar atmosphere.The reaction mixture was cooled, then the precipitates were filtered off through Celite and water (50 mL) was added to the filtrate. After the two layers were separated, the water layer was extracted with CH2Cl2 and the organic layer was dried over potassium carbonate and concentrated. The residue was purified via recrystallization from toluene to give 4,4'-oxybis(biphenyl-4-carbaldehyde) as a white solid (548 mg, 16% yield). Mp >300 C; 1HNMR (CDCl3) d 7.17 (d, J = 8.8 Hz, 4H), 7.65 (d, J = 8.8 Hz, 4H),7.75 (d, J = 8.4 Hz, 4H), 7.96 (d, J = 8.4 Hz, 4H), 10.06 (s, 2H); 13CNMR (CDCl3) d 119.4, 127.4, 128.9, 129.8, 130.3, 135.1, 146.3,157.4, 191.8; IR(cm1): 2924, 2854, 1901, 1692, 1601, 1524,1491, 1460, 1377, 1276, 1177, 1118, 817; Anal. Calcd forC26H18O3: C, 82.52; H, 4.79. Found: C, 82.58; H, 4.52.
  • 61
  • [ 2050-47-7 ]
  • [ 87199-17-5 ]
  • C64H56N4O2 [ No CAS ]
  • 62
  • [ 16632-21-6 ]
  • [ 87199-17-5 ]
  • C12H10BN3O6 [ No CAS ]
  • 64
  • [ 4877-80-9 ]
  • [ 87199-17-5 ]
  • C39H21B3O9 [ No CAS ]
  • 65
  • [ 87199-17-5 ]
  • [ 579475-29-9 ]
  • 4-(6-cyclopropyl-3-pyridinyl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.81 g With potassium phosphate; palladium diacetate; In ethylene glycol; at 80℃; for 3h; Reference Example 6-6 4-(6-Cyclopropyl-3-pyridinyl) benzaldehyde A mixture of <strong>[579475-29-9]3-bromo-6-(cyclopropyl)pyridine</strong> (2.00 g), 4-formylphenylboronic acid (1.82 g), palladium(II) acetate (113 mg), tripotassium phosphate (4.50 g) and ethylene glycol (16.8 mL) was stirred at 80C for 3 hours. After cooling the reaction mixture to room temperature, water was added to it and two extractions were conducted with ethyl acetate. The combined organic layers were washed with saturated brine and thereafter the crude product was adsorbed on diatomaceous earth, with the solvent being distilled off under reduced pressure. The crude product adsorbed on the diatomaceous earth was purified by silica gel column chromatography (hexane:ethyl acetate = 98:2-50:50) to give the titled compound as a colorless solid (1.81 g). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.00 - 1.17 (m, 4 H) 2.03 - 2.16 (m, 1 H) 7.21 - 7.30 (m, 1 H) 7.66 - 7.83 (m, 3 H) 7.93 - 8.01 (m, 2 H) 8.68 - 8.76 (m, 1 H) 10.06 (s, 1 H). MS ESI/APCI Dual posi: 224[M+H]+.
  • 66
  • [ 87199-17-5 ]
  • [ 194416-45-0 ]
  • 2-((4'-(bis(4-methoxyphenyl)amino)biphenyl-4-yl)methylene)malononitrile [ No CAS ]
  • 67
  • [ 87199-17-5 ]
  • [ 194416-45-0 ]
  • C27H23NO3 [ No CAS ]
  • 68
  • [ 40000-20-2 ]
  • [ 87199-17-5 ]
  • 4-(1,10-phenanthrolin-6-yl)benzaldehyde [ No CAS ]
  • 69
  • [ 27992-32-1 ]
  • [ 87199-17-5 ]
  • C12H9NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; for 16h;Inert atmosphere; Reflux; General procedure for the synthesis of 01To a stirred solution of 2-bromo-6-hydroxypyridine (100 mg, 0.57 mmol) and 4-fomiylphenylboronic acid (72 mg, 0.48 mmol) in DME (2 mL) were added Pd(PPh3)4 (55 mg,0.05 mmol) and Na2CO3 solution (0.63 mL, 2M). The mixture was stuffed under N2atmosphere maintaining gentle reflux for 16 hours. The mixture was diluted with water (10mL) extracted with EtOAc (20 mLx3). The combined extracts were washed with brine (20mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford a crude,which was purified by combi flash (eluent: EtOAc) to afford 01.
  • 70
  • [ 1000623-95-9 ]
  • [ 87199-17-5 ]
  • 4,4'-(5,5'-(2,5-bis(2-ethylhexyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(thiophen-5,2-diyl))dibenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water;Inert atmosphere; Reflux; Under N2 atmosphere, the mixture of compound DPP-Br2 (100mg, 0.146mmoles), 4-formylphenylboronicacid (89.6mg, 0.6mmoles), Pd(PPh3)4 (20mg, 0.017mmole), 2M aqueous solution of Na2CO3 (3mL) in dry THF (15mL) was refluxed overnight. The reaction mixture was extracted with DCM, and washed with water and brine solutions. The organic layer was dried with anhydrous Na2SO4 and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel using Hexane and ethylacetate in the ratio of 10: 2 (v/v) as eluent to afford DPP-B-CHO Yield: 80.0%. 1H NMR (500MHz, CHCl3) delta 10.04 (s, 2H), 8.98-8.97 (d, J=4.1Hz, 2H), 7.95-7.94 (d, J=8.3Hz, 4H), 7.84-7.83 (d, J=8.2Hz, 4H), 7.61-7.58 (d, J=6.2Hz, 2H), 4.09 (t, J=7.2Hz, 4H), 1.40 (m, 9H), 1.30-1.16 (m, 7H), 1.01-0.89 (m, 7H), 0.89 (m, 7H). MALDI-TOF MS Calcd. for733.0; Found 733.71.
  • 71
  • [ 937013-66-6 ]
  • [ 87199-17-5 ]
  • 3′-(1H-imidazol-2-yl)-4-biphenylcarbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; for 1.83333h;Inert atmosphere; General procedure: A mixture of 4-bromobenzaldehyde (2.78 g; 15.0 mmol), [3-(aminocarbonyl)-phenyl]boronic acid (2.72 g; 16.5 mmol), PdCl2(dppf).CH2Cl2(0.306 g; 0.38 mmol), DME (25 mL) and Na2CO3(25 mL of a 2M solution) was sparged 20 min with N2and heated under reflux for 90 min (consumption of aryl bromide observed by LC/MS). Upon cooling, the mixture was partitioned between EtOAc/H2O, layers were separated, and the aqueous layer was extracted with EtOAc (×2). Combined organics were washed (H2O, brine), dried over Na2SO4and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a tan solid. Used IV-21 and 4- formylphenyl boronic acid Note 1, 2. Note 1 Used 4:1 v/v PhMe/EtOH as organic cosolvents (instead of DME).Note 2 Used Pd(PPh3)4as catalyst (instead of PdCl2(dppf).CH2Cl2).
  • 72
  • [ 87199-17-5 ]
  • [ 474918-32-6 ]
  • C55H42N2 [ No CAS ]
  • 73
  • [ 156573-09-0 ]
  • [ 87199-17-5 ]
  • [ 1078729-28-8 ]
YieldReaction ConditionsOperation in experiment
92.9% With potassium phosphate; In 1,4-dioxane; for 2h;Reflux; Inert atmosphere; 4-Formylphenylboronic acid (s47) (75.9 g),4-bromo-2,3-difluoroethoxybenzene (s48) (100.0 g), potassium phosphate (269.0g), dichlorobistriphenylphosphinepalladium (II) (Pd(Ph3P)2Cl2;8.9 g) and 1,4-dioxane (500 ml) were placed in a reaction vessel under an atmosphere of nitrogen, and the mixture was heated to reflux for 2 hours. After the reaction mixture had been cooled to 25 C, it was treated with water,and the aqueous layer was extracted with toluene. The combined organic layers were washed with water,and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by column chromatography with toluene as an eluent and silica gel as a stationary phase powder. The product was purified by recrystallization from a mixed solvent of heptane and toluene (heptane:toluene=l: 1 by volume) to give 4-ethoxy-4'-formyl-2,3-difluoro-l,l'-biphenyl (s49) (102.8g). The yield based on the compound (s48) was 92.9%.
  • 74
  • [ 63525-48-4 ]
  • [ 87199-17-5 ]
  • C22H14O4 [ No CAS ]
  • 75
  • [ 66191-86-4 ]
  • [ 87199-17-5 ]
  • methyl 3-(4'-formyl-2-biphenylyl)propanoate [ No CAS ]
  • 76
  • [ 88-12-0 ]
  • [ 383-62-0 ]
  • [ 87199-17-5 ]
  • ethyl 2,2-difluoro-4-(4-formylphenyl)-4-(2-oxopyrrolidin-1-yl)butanoate [ No CAS ]
  • 77
  • [ 608-33-3 ]
  • [ 87199-17-5 ]
  • C20H14O3 [ No CAS ]
  • 78
  • [ 5981-09-9 ]
  • [ 87199-17-5 ]
  • C39H33B3N4O6 [ No CAS ]
  • 79
  • [ 1003-09-4 ]
  • [ 87199-17-5 ]
  • [ 107834-03-7 ]
YieldReaction ConditionsOperation in experiment
89% 2-bromothiophene (0.489 g, 3 mmol),4-formylphenylboronic acid (0.60 g, 4 mmol), K2CO3 (0.696 g, 1 N) and N,N-dimethylformamide (20 mL) were placed in a 100 mL three-neck flask. After mixing for 30 minutes under N2 protection, tetrakis(triphenylphosphine)palladium (0.115 g, 0.1 mmol) was added.The reaction was stirred at 90 C for 6 hours. It was naturally cooled to ambient temperature, and the crude product was dissolved in dichloromethane and washed with water (100ml). The organic solution was dried over MgSO 4 to remove water. The final product was recrystallized from ethyl acetate. Obtained a yellow solid of 0.46 g.The yield was 89%.
87% General procedure: A solution of Pd(OAc)2 (0.05 eq.) and PPh3 (0.2 eq.) in toluene was stirred at r.t. under an argonatmosphere for 10 mins. After that, the solution of an appropriate aryl-bromide (1 eq.), an appropriatearylboronic acid (1.1 eq.) and 2M aq. Na2CO3 (2 eq.) in MeOH and toluene was added. The mixturewas stirred at 110 C under an argon atmosphere for 3 h. The reaction work up method is provided foreach compound.
  • 80
  • [ 2050-47-7 ]
  • [ 87199-17-5 ]
  • C19H13BrO2 [ No CAS ]
  • 81
  • [ 87199-17-5 ]
  • [ 84322-56-5 ]
  • 1,3,5-trifluoro-2,4,6-tris(4-formylphenyl)benzene [ No CAS ]
  • 82
  • [ 1127-76-0 ]
  • [ 87199-17-5 ]
  • C19H16O [ No CAS ]
  • 83
  • [ 141-30-0 ]
  • [ 87199-17-5 ]
  • [ 914349-19-2 ]
YieldReaction ConditionsOperation in experiment
25% With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃; 3,6-dichloropyridazine (400 mg, 2.69 mmol) was dissolved in dioxane (6 mL) and distilled water (2 mL)After dissolving, 4-formyl phenylboronic acid (321 mg, 2.15 mmol),Potassium carbonate (920 mg, 6.71 mmol),PdCl2 (dppf) 2 (110 mg, 0.13 mmol) was added to a solution ofAnd stirred at 90 C.The reaction mixture was diluted with dichloromethane, washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Purification by column chromatography (40% EtOAc / Hexane) provided 4- (6-chloropyridazin-3-yl) benzaldehyde (148 mg, 25%) as a white solid.
  • 84
  • [ 7752-78-5 ]
  • [ 87199-17-5 ]
  • 4-(2-methylpyrimidin-5-yl)benzaldehyde [ No CAS ]
  • 85
  • [ 87199-17-5 ]
  • [ 57103-20-5 ]
  • C32H21NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68.24% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; toluene; at 90℃;Inert atmosphere; B.Compound <strong>[57103-20-5]3,6-dibromo-9-phenylcarbazole</strong> (157.7 mg, 0.40 mmol)4-formylphenylboronic acid (129.7 mg, 0.87 mmol),Bis (triphenylphosphine) palladium dichloride Pd (PPh3) 2Cl2 (28.1 mg, 0.04 mmol)Was dissolved in 40 mL of a mixed solution of toluene and tetrahydrofuran (Vtoluene: VTHF = 1: 1)The reaction was refluxed at 90 ° C under nitrogen,Thin layer chromatography to the reaction is complete.After the resulting solution was spin off the organic solvent,Extracted with ethyl acetate,Organic layer washed three times,Saturated NaCl solution once,Dried over anhydrous sodium sulfate,The solvent is evaporated under reduced pressure;The crude product was passed through a column of petroleum ether and ethyl acetate mixed solvent (20: 1)4,4 '- (9-phenyl-9H-carbazole-3,6-diyl) benzaldehyde(Yellow powder, 123.1 mg, yield 68.24percent).
  • 86
  • [ 4181-20-8 ]
  • [ 87199-17-5 ]
  • 4',4''',4'''''-nitrilotris(([1,1'-biphenyl]-4-carbaldehyde)) [ No CAS ]
  • 87
  • [ 1273-82-1 ]
  • [ 87199-17-5 ]
  • 4-((ferrocenylimino)methyl)phenylboronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; toluene; General procedure: Aminoferrocene (1, 11.0 mg, 0.0547 mmol) was dissolved in 9 cm3 toluene. Formylphenylboronic acid (2, 8.2 mg,0.0547 mmol) was dissolved in 1 cm3 dry ethanol. Both reagent solutions were mixed in an evaporating flask. The solvents were removed under reduced pressure on a rotary vacuum evaporator (the water bath temperature strictly below 40 C) to give [(ferrocenylimino)methyl]phenylboronic acid 3 as a violet/red powder; 18.2 mg (quant.). The products were used as prepared without need of a further purification (Fig. 5).
  • 88
  • [ 625-95-6 ]
  • [ 87199-17-5 ]
  • [ 400744-83-4 ]
YieldReaction ConditionsOperation in experiment
71.3% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In water; acetonitrile; at 20℃; 3-Iodotoluene (0.87 g, 4 mmol), 4-formylphenylboronicacid (0.72 g, 4.8 mmol), K2CO3 (2.0 g, 14.4 mmol)and [P(Ph)3]2PdCl2 (85 mg, 0.121 mmol) weretaken in 100 mL single neck round bottom flask, added 10:10 mLwater-acetonitrile. The reaction mixture was stirred at room temperature overnight.And the reaction was monitored by thin-layer chromatography (TLC). After thereaction completed, the reaction mixture was filtered. The filtrate wasextracted with EtOAc (15 mL x 3). Thecombined organic layer was dried on anhydrous Na2SO4 and concentrated;the crude product was purified by column chromatography over silica gel toafford target product with high yield of 71.3%.
  • 89
  • [ 61326-44-1 ]
  • [ 87199-17-5 ]
  • 4',4''',4''''',4'''''''-(ethene-1,1,2,2-tetrayl)tetrakis(([1,1'-biphenyl]-4-carbaldehyde)) [ No CAS ]
  • 90
  • [ 87199-17-5 ]
  • [ 144981-85-1 ]
  • C22H18O [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 85℃; for 24h;Inert atmosphere; To a 100 ml three-neck flask, was sequentially added <strong>[144981-85-1]9,9-dimethyl-2-iodofluorene</strong> (0.96 g, 3.0 mmol), 4-formylphenylboronic acid (0.63 g, 4.2 mmol), tetrakis(triphenylphosphine)palladium (0.17 g, 0.15 mmol), THF (40 ml) and K2CO3 aqueous solution (20 ml, 2 M), the system vacuum, argon protection, the temperature at 85 °C reflux reaction 24 h. Stopping the reaction, cooling to room temperature, poured into 100 ml distilled water, extracted with ethyl acetate (50 ml × 3), organic phase among ordinary and common salt is washed with water (50 ml × 3), anhydrous Na2SO4Drying overnight. Filtering and collecting the filtrate, the solvent evaporate under reduced pressure, the residue using silica gel (200 - 300 mesh) column chromatography [eluant, V (petroleum ether): V (ethyl acetate)=20:1] purification gets yellow solid intermediate 2 (0.82 g), yield 92percent.
  • 91
  • [ 87199-17-5 ]
  • [ 144981-85-1 ]
  • C62H57BF2N2 [ No CAS ]
  • 92
  • [ 87199-17-5 ]
  • [ 283173-50-2 ]
  • 93
  • [ 1151802-23-1 ]
  • [ 87199-17-5 ]
  • 4-(1-cyclopropyl-1H-pyrazol-4-yl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; potassium carbonate; catacxium A; In 1,4-dioxane; water; at 100℃;Inert atmosphere; Sealed tube; General procedure: A suspension of 1 -Difluoromethyl-4-(4,4,5,5 -tetramethyl-[ 1,3,21 dioxaborolan-2-yl)- 1H-pyrazole (1.47 g, 6.03 mmol), 4-bromo-2,6-difluorobenzaldehyde (1.1 g, 4.98 mmol), palladium acetate (0.03 g, 0.12 mmol), butyldi-1-adamantylphosphine (0.11 g, 0.3 mmol), and potassium carbonate (2.06 g, 14.93 mmol) in water (7 ml) and 1,4-dioxane (22 ml) in a tube was degassedfor 10 mm with argon, then the tube was sealed and heated at 100 C overnight. The reaction mixture was cooled to room temperature, concentrated under reduce pressure, the residue was diluted with EtOAc and washed with brine 2x then dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (10% to 25% EtOAc/Hex) to afford P7. 1HNMR (400 MHz, Chloroform-d) oe 10.32 (s, 1H), 8.16 (s,1H), 7.96 (s, 1H), 7.23 (t, J = 60.4 Hz, 1H), 7.14 (d, J = 9.5 Hz, 2H).
  • 94
  • [ 10016-52-1 ]
  • [ 87199-17-5 ]
  • C26H16O3 [ No CAS ]
  • 95
  • [ 6165-68-0 ]
  • [ 1295502-53-2 ]
  • [ 87199-17-5 ]
  • 4-(4-formylphenyl)-7-(thiophene-2-yl)-5,6-difluoro-2,1,3-benzothiadiazole [ No CAS ]
  • 96
  • [ 462-08-8 ]
  • [ 4482-01-3 ]
  • [ 87199-17-5 ]
  • [ 127406-55-7 ]
YieldReaction ConditionsOperation in experiment
78% General procedure: In a oven-dried flask and under nitrogen flow, benzenediazonium o-benzenedisulfonimide (1a, 161mg, 0.5mmol) was added to a suspension of 4-methoxyphenylboronic acid (3a, 91mg, 0.6mmol), [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) (2:1) toluene adduct (39mg, 0.025mmol, 5mol%), Cs2CO3 (325mg, 1mmol) in THF (5mL). The resulting mixture was stirred at room temperature for 2h; the completion of the reaction was confirmed by the absence of azo coupling with 2-naphthol. Then, the reaction mixture was poured into diethyl ether/water (100mL, 1:1). The aqueous layer was separated and extracted with diethyl ether (50mL). The combined organic extracts were washed with water (50mL), dried with Na2SO4 and evaporated under reduced pressure. GC-MS analyses of the crude residue showed 4-methoxybiphenyl (4a), MS (EI): m/z 184 (M+) as the major product, besides traces of biphenyl, MS (EI): m/z 154 (M+), 4,4'-dimethoxybiphenyl, MS (EI): m/z 214 (M+), N-phenyl-o-benzenedisulfonimide, MS (EI): m/z 295 (M+). The crude residue was purified on a short column, eluting with petroleum ether/diethyl ether (9:1). The only isolated product was the title compound (4a, 81mg, 88% yield).
  • 97
  • [ 426-65-3 ]
  • [ 87199-17-5 ]
  • [ 884602-82-8 ]
  • 98
  • [ 3034-52-4 ]
  • [ 87199-17-5 ]
  • [ 198904-53-9 ]
  • 99
  • [ 23488-38-2 ]
  • [ 87199-17-5 ]
  • 1,2,4,5-tetrakis-(4-formylphenyl)-3,6-dimethylbenzene [ No CAS ]
  • 100
  • [ 62484-31-5 ]
  • [ 87199-17-5 ]
  • 7-methoxy-2,4-bis(4-formylphenyl)quinazoline [ No CAS ]
  • 101
  • [ 41731-23-1 ]
  • [ 87199-17-5 ]
  • [ 1344734-15-1 ]
YieldReaction ConditionsOperation in experiment
96% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 2h;Inert atmosphere; [0233] To a solution of 2-bromo-5-methyl-l,3-thiazole (300 mg, 1.68 mmol, 1.0 equiv) in a mixture of dioxane/water (50/10 mL) were added Pd(dppf)Cl2.CH2Cl2 (138 mg, 0.17 mmol, 0.1 equiv) and potassium carbonate (465 mg, 3.36 mmol, 2.00 equiv) under nitrogen atmosphere. The mixture was stirred at 80 C for 2 h, cooled to r.t, and added water (60 mL). The aqueous layer was extracted with ethyl acetate (30 mL) three times. The combined organic layers were dried over Na2S04, concentrated under reduced pressure, and purified by silica gel column with ethyl acetate/petroleum ether (1/10) to give 330 mg (96%) of 4-(5- methyl-l,3-thiazol-2-yl)benzaldehyde as a yellow solid. LRMS (ES) m/z 204 (M+H).
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Chemical Structure| 870777-33-6

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(3-Formyl-5-methylphenyl)boronic acid

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Chemical Structure| 40138-16-7

[ 40138-16-7 ]

(2-Formylphenyl)boronic acid

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Chemical Structure| 149104-90-5

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4-Acetylphenylboronic acid

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Chemical Structure| 204841-19-0

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3-Acetylphenylboronic acid

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Aryls

Chemical Structure| 87199-16-4

[ 87199-16-4 ]

(3-Formylphenyl)boronic acid

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Chemical Structure| 870777-33-6

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(3-Formyl-5-methylphenyl)boronic acid

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Chemical Structure| 40138-16-7

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(2-Formylphenyl)boronic acid

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Chemical Structure| 149104-90-5

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4-Acetylphenylboronic acid

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Chemical Structure| 204841-19-0

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3-Acetylphenylboronic acid

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Aldehydes

Chemical Structure| 87199-16-4

[ 87199-16-4 ]

(3-Formylphenyl)boronic acid

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Chemical Structure| 870777-33-6

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(3-Formyl-5-methylphenyl)boronic acid

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Chemical Structure| 40138-16-7

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(2-Formylphenyl)boronic acid

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Chemical Structure| 1256355-30-2

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(5-Fluoro-2-formylphenyl)boronic acid

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Chemical Structure| 913835-76-4

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4-Chloro-2-formylphenylboronic acid

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